##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
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# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-02-12
_journal_date_accepted     2008-02-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     o724
_journal_page_last     o724
_journal_paper_category     QO
_journal_coeditor_code     LH2597
_publ_contact_author
;
    Siddiqui, Hamid Latif'
    Institute of Chemistry
    University of the Punjab
    Lahore
    Pakistan
;
_publ_contact_author_email     parvez@ucalgary.ca
_publ_contact_author_fax     ' (403)289-9488 '
_publ_contact_author_phone     ' (403)220-5348 '
_publ_section_title
;
2-Methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
;
loop_
    _publ_author_name
    _publ_author_address
    'Siddiqui, Waseeq Ahmad'
; Department of Chemistry
University of Sargodha
Sargodha
Pakistan
;
    'Ahmad, Saeed'
; Department of Chemistry
University of Science and Technology
Bannu
Pakistan
;
    'Siddiqui, Hamid Latif'
; Institute of Chemistry
University of the Punjab
Lahore
Pakistan
;
    'Parvez, Masood'
; Department of Chemistry
The University of Calgary
2500 University Drive NW
Calgary
Alberta
Canada T2N 1N4
;
data_I
_chemical_name_systematic
;
2-Methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C8 H7 N O3 S'
_chemical_formula_sum     'C8 H7 N O3 S'
_chemical_formula_iupac     'C8 H7 N O3 S'
_chemical_formula_weight     197.21
_chemical_melting_point     '?'
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/m '
_symmetry_space_group_name_Hall     '-P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
    '-x, -y, -z'
    'x, -y-1/2, z'
_cell_length_a     7.463(7)
_cell_length_b     6.761(6)
_cell_length_c     8.748(8)
_cell_angle_alpha     90.00
_cell_angle_beta     103.78(3)
_cell_angle_gamma     90.00
_cell_volume     428.7(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1724
_cell_measurement_theta_min     3.23
_cell_measurement_theta_max     27.42
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.12
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.528
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     204
_exptl_absorpt_coefficient_mu     0.348
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1997)'
_exptl_absorpt_correction_T_min     0.9595
_exptl_absorpt_correction_T_max     0.9761
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1724
_diffrn_reflns_av_R_equivalents     0.0234
_diffrn_reflns_av_sigmaI/netI     0.0365
_diffrn_reflns_theta_min     3.23
_diffrn_reflns_theta_max     27.42
_diffrn_reflns_theta_full     27.42
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     1045
_reflns_number_gt     889
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0510
_refine_ls_R_factor_gt     0.0408
_refine_ls_wR_factor_gt     0.0999
_refine_ls_wR_factor_ref     0.1063
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     1045
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0455P)²+0.2966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.405
_refine_diff_density_min     -0.419
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1998)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SAPI91 (Fan, 1991)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.68037(10) 0.2500 0.26611(7) 0.0314(2) Uani d S 1 . .
    O O1 0.2425(3) 0.2500 0.4038(3) 0.0416(5) Uani d S 1 . .
    O O2 0.7324(2) 0.0698(2) 0.20266(16) 0.0445(4) Uani d . 1 . .
    N N1 0.4534(3) 0.2500 0.2520(3) 0.0314(5) Uani d S 1 . .
    C C1 0.7314(4) 0.2500 0.4722(3) 0.0254(5) Uani d S 1 . .
    C C2 0.9043(4) 0.2500 0.5750(3) 0.0337(6) Uani d S 1 . .
    H H2 1.0141 0.2500 0.5381 0.040 Uiso calc SR 1 . .
    C C3 0.9090(4) 0.2500 0.7337(3) 0.0403(7) Uani d S 1 . .
    H H3 1.0249 0.2500 0.8079 0.048 Uiso calc SR 1 . .
    C C4 0.7486(4) 0.2500 0.7873(3) 0.0379(7) Uani d S 1 . .
    H H4 0.7566 0.2500 0.8974 0.045 Uiso calc SR 1 . .
    C C5 0.5767(4) 0.2500 0.6832(3) 0.0308(6) Uani d S 1 . .
    H H5 0.4670 0.2500 0.7203 0.037 Uiso calc SR 1 . .
    C C6 0.5690(3) 0.2500 0.5235(3) 0.0251(5) Uani d S 1 . .
    C C7 0.4012(4) 0.2500 0.3931(3) 0.0289(6) Uani d S 1 . .
    C C8 0.3218(5) 0.2500 0.0986(3) 0.0455(8) Uani d S 1 . .
    H H8A 0.1982 0.2500 0.1130 0.055 Uiso d SR 1 . .
    H H8B 0.3405 0.1341 0.0410 0.055 Uiso d R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0415(4) 0.0319(4) 0.0237(3) 0.000 0.0133(3) 0.000
    O1 0.0284(10) 0.0449(13) 0.0521(13) 0.000 0.0107(9) 0.000
    O2 0.0587(10) 0.0435(9) 0.0369(8) 0.0058(7) 0.0223(7) -0.0101(7)
    N1 0.0355(12) 0.0301(12) 0.0266(11) 0.000 0.0031(9) 0.000
    C1 0.0319(13) 0.0222(12) 0.0237(12) 0.000 0.0099(10) 0.000
    C2 0.0276(13) 0.0367(16) 0.0371(14) 0.000 0.0085(11) 0.000
    C3 0.0402(16) 0.0417(17) 0.0340(15) 0.000 -0.0010(12) 0.000
    C4 0.0553(18) 0.0343(16) 0.0238(13) 0.000 0.0087(12) 0.000
    C5 0.0392(15) 0.0257(13) 0.0324(14) 0.000 0.0181(12) 0.000
    C6 0.0280(12) 0.0189(12) 0.0297(13) 0.000 0.0093(10) 0.000
    C7 0.0330(14) 0.0221(13) 0.0320(13) 0.000 0.0086(11) 0.000
    C8 0.0551(19) 0.0452(19) 0.0284(15) 0.000 -0.0053(13) 0.000
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 4_565 1.430(2) ?
    S1 O2 . 1.430(2) ?
    S1 N1 . 1.668(3) ?
    S1 C1 . 1.752(3) ?
    O1 C7 . 1.211(3) ?
    N1 C7 . 1.380(4) ?
    N1 C8 . 1.462(4) ?
    C1 C2 . 1.386(4) ?
    C1 C6 . 1.389(4) ?
    C2 C3 . 1.380(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.386(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.385(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.384(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.479(4) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O2 4_565 . 116.79(14) ?
    O2 S1 N1 4_565 . 109.63(8) ?
    O2 S1 N1 . . 109.63(8) ?
    O2 S1 C1 4_565 . 112.76(8) ?
    O2 S1 C1 . . 112.76(8) ?
    N1 S1 C1 . . 92.54(12) ?
    C7 N1 C8 . . 123.3(2) ?
    C7 N1 S1 . . 115.6(2) ?
    C8 N1 S1 . . 121.1(2) ?
    C2 C1 C6 . . 122.7(2) ?
    C2 C1 S1 . . 127.5(2) ?
    C6 C1 S1 . . 109.9(2) ?
    C3 C2 C1 . . 116.7(3) ?
    C3 C2 H2 . . 121.6 ?
    C1 C2 H2 . . 121.6 ?
    C2 C3 C4 . . 121.6(3) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 121.1(3) ?
    C5 C4 H4 . . 119.5 ?
    C3 C4 H4 . . 119.5 ?
    C6 C5 C4 . . 118.2(2) ?
    C6 C5 H5 . . 120.9 ?
    C4 C5 H5 . . 120.9 ?
    C5 C6 C1 . . 119.7(2) ?
    C5 C6 C7 . . 127.0(2) ?
    C1 C6 C7 . . 113.2(2) ?
    O1 C7 N1 . . 124.0(3) ?
    O1 C7 C6 . . 127.2(3) ?
    N1 C7 C6 . . 108.8(2) ?
    N1 C8 H8A . . 109.6 ?
    N1 C8 H8B . . 109.4 ?
    H8A C8 H8B . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2 S1 N1 C7 4_565 . . . -115.28(8) ?
    O2 S1 N1 C7 . . . . 115.28(8) ?
    C1 S1 N1 C7 . . . . 0.0 ?
    O2 S1 N1 C8 4_565 . . . 64.72(8) ?
    O2 S1 N1 C8 . . . . -64.72(8) ?
    C1 S1 N1 C8 . . . . 180.0 ?
    O2 S1 C1 C2 4_565 . . . -67.46(9) ?
    O2 S1 C1 C2 . . . . 67.46(9) ?
    N1 S1 C1 C2 . . . . 180.0 ?
    O2 S1 C1 C6 4_565 . . . 112.54(9) ?
    O2 S1 C1 C6 . . . . -112.54(9) ?
    N1 S1 C1 C6 . . . . 0.0 ?
    C6 C1 C2 C3 . . . . 0.0 ?
    S1 C1 C2 C3 . . . . 180.0 ?
    C1 C2 C3 C4 . . . . 0.0000(10)
                                 ?
    C2 C3 C4 C5 . . . . 0.0000(10)
                                 ?
    C3 C4 C5 C6 . . . . 0.0000(10)
                                 ?
    C4 C5 C6 C1 . . . . 0.0 ?
    C4 C5 C6 C7 . . . . 180.0 ?
    C2 C1 C6 C5 . . . . 0.0 ?
    S1 C1 C6 C5 . . . . 180.0 ?
    C2 C1 C6 C7 . . . . 180.0 ?
    S1 C1 C6 C7 . . . . 0.0 ?
    C8 N1 C7 O1 . . . . 0.0 ?
    S1 N1 C7 O1 . . . . 180.0 ?
    C8 N1 C7 C6 . . . . 180.0 ?
    S1 N1 C7 C6 . . . . 0.0 ?
    C5 C6 C7 O1 . . . . 0.0 ?
    C1 C6 C7 O1 . . . . 180.0 ?
    C5 C6 C7 N1 . . . . 180.0 ?
    C1 C6 C7 N1 . . . . 0.0 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C8 H8A O1 . 0.96 2.49 2.869(4) 104
    C2 H2 O1 1_655 0.95 2.29 3.227(4) 169
    C8 H8B O2 3_655 0.96 2.49 3.358(3) 151
